SVP, Chief Actuary at Clearcover (Chicago, IL or Remote)

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Our Value Proposition: Clearcover is a venture-backed technology start-up disrupting the trillion-dollar legacy insurance market. We’ve focused on building products that create confident, happy customers - and we’re flourishing. We believe in putting our people first, paying them well, and working together to solve tough problems. If you’d like a high-growth opportunity with an award-winning company, let’s chat.

In this role: The Chief Actuary holds comprehensive management and oversight of Clearcover’s actuarial function including advancing the core pillars of rate adequacy, reserving, and lifetime value modeling. Core responsibilities include managing and monitoring the risk profile for the enterprise by being an advisor to the office of the CFO on reinsurance and catastrophe management. 

This role will drive and refine portfolio level reserving policy and will establish a partnership grounded in trust and transparency with Claims leadership.

The Chief Actuary is a key stakeholder in the strategic development and planning process for the enterprise.  This role leads the development and continuous enhancement of all relevant Insurance P&L inputs to the financial operating models. The Chief Actuary is charged with driving the company’s achievement of financial targets grounded in actuarial support and while maintaining a balance with its revenue and risk management goals.

This role is a key business partner to Claims, Finance, Product Management, Revenue, Servicing, and Technology at a tactical and strategic level. This role leads the development and continuous enhancement of all relevant Insurance P&L inputs to the financial operating models. 

What will you be doing?

  • Deliver a long term vision for the function within the first hundred days.
  • Complete a thorough review of existing actuarial strategy in the first hundred days to ascertain effectiveness.
  • Build a world class actuarial culture which achieves high standards of technical excellence and leverages technology to drive portfolio level measurements where possible.
  • Set, drive and execute an ambitious innovation roadmap for reserving, rate adequacy, and lifetime value modeling. 
  • Motivate the team to stay curious and current on industry trends and the competitive landscape. Collaborate cross functionally to ensure knowledge sharing on market trends.
  • Function as an everyday partner with claims leadership.
  • Provide regular updates to investors and reinsurers, as necessary.
  • Be a steward of our Leadership Principles and ensure the team lives by them every day.
  • Serve as a credible, knowledgeable and trusted resource to the senior leadership team.

What will you bring?

  • Actuarial Fellow Designation (FCAS) and Member of the American Academy of Actuaries (MAAA) required.
  • Senior leadership or Executive level experience in a rapid growth environment.
  • Extensive experience in a management role.
  • Ability to quickly gain thorough knowledge of the company (internal and external) and its products.
  • A willingness to examine every opportunity from first principles and challenge long-held assumptions about insurance and actuarial best practices.
  • Property and Casualty insurance experience required with a strong emphasis on reserving and reinsurance.
  • A deep understanding of property-casualty insurance including product management and distribution channel nuances.
  • Strong communication skills, verbal and written, with a variety of audiences at all levels, both internal and external.
  • Ability to successfully lead a diverse team.
  • Excellent project management and relationship building capabilities.

But wait, there’s more: As a people-first company, your health and well-being is a priority at Clearcover. While we do offer medical (and cover the vast majority of the premium), dental, vision (and cover 100% of those premiums), and 401K (we contribute 3% even if you contribute nothing), we’ve curated a stack of perks and benefits that stretch beyond the expected. With over half of our employees remote to the Chicago HQ office, we paved the way for flexible work locations and continue to offer this flexibility. Our people also have access to unlimited vacation, monthly mental health workshops, discounted gym memberships, equity in the company, and an annual bonus program. Plus, if Clearcover is available in your state, you could have access to an employee discount on auto insurance! Excited to learn more? Complete the application below!

Clearcover is an Equal Opportunity Employer (EOE) that welcomes and encourages all applicants to apply regardless of age, race, color, religion, sex, sexual orientation, gender identity and/or expression, national origin, disability, veteran status, marital or parental status, ancestry, citizenship status, pregnancy or other reasons prohibited by law.

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Technology we use

  • Engineering
    • KotlinLanguages
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    • ScalaLanguages
    • ReactLibraries
    • Ruby on RailsFrameworks
    • SnowflakeDatabases


33 W Monroe, Chicago, IL 60603

What are Clearcover Perks + Benefits

Clearcover Benefits Overview

Clearcover offers a comprehensive benefits package along with a number of perks in an effort to support our employees and their families. We work to align our perks with our core values and empower our employees to balance work and their personal lives.

Volunteer in local community
Intracompany committees
Daily sync
Open door policy
Team owned deliverables
Team based strategic planning
Pair programming
Open office floor plan
Dedicated Diversity/Inclusion Staff
Unconscious bias training
Hiring Practices that Promote Diversity
Health Insurance & Wellness Benefits
Flexible Spending Account (FSA)
Disability Insurance
Dental Benefits
Clearcover covers 100% of the employee's dental benefits.
Vision Benefits
Clearcover covers 100% of the employee's vision benefits.
Health Insurance Benefits
Clearcover's health insurance plan is with United Healthcare with a range of plans including PPO, HDHP and HSA. If you elect an HSA, we cover your out-of-pocket deductible as an HSA contribution.
Life Insurance
Clearcover offers voluntary life insurance.
Pet Insurance
Wellness Programs
Onsite Gym
Team workouts
Virtual yoga classes offered twice per week!
Mental Health Benefits
Monthly Mental Health Workshops 1:1 Counseling sessions with a LCSW Live, virtual yoga, 3 x week Unlimited vacation Meeting-free Fridays Access to supportive mental health community in Slack
Retirement & Stock Options Benefits
401(K) Matching
Clearcover provides employees with a 401(k) contribution of 3% of an employee's annual gross pay.
Company Equity
Performance Bonus
Annual bonus based upon company performance
Child Care & Parental Leave Benefits
Child Care Benefits
Dependent Care FSA allows you to put away pre-tax dollars towards daycare expenses for dependents under the age of 13.
Generous Parental Leave
Clearcover offers parental leave for new parents after birth or adoption of a child. Full-time employees that have been employed for six months are eligible for six weeks of paid Parental Leave.
Flexible Work Schedule
Clearcover has flexible start and end times based upon your position and your team.
Remote Work Program
Our remote work program includes work from home Full-time remote for specific positions, as well as work flexible remote work for most position.
Family Medical Leave
Employees who have been with the company for 12 months are eligible for 12 weeks of family medical leave. Other policies apply to those here less than 12 months.
Return-to-work program post parental leave
Vacation & Time Off Benefits
Unlimited Vacation Policy
Paid Volunteer Time
Paid Holidays
Paid Sick Days
Employees receive 5 paid sick days each year.
Perks & Discounts
Casual Dress
Commuter Benefits
Clearcover's offers Commuter Benefits, employees can save an average of 30 percent off their commute by contributing pre-tax dollars.
Company Outings
Clearcover celebrates company wins by organizing quarterly outings to a variety of places like the Escape Room, Punchbowl Social and Bounce.
Game Room
Clearcover's game room includes a state-of-the-art ping pong table, custom Nerf gun wall and a Pop-a-Shot to let employees enjoy breaks between work.
Stocked Kitchen
We send snack boxes monthly since we are virtual.
Home Office Stipend for Remote Employees
We offer a one-time $250 stipend to set up your work from home office. Use this for anything that will support your work from home arrangement.
Professional Development Benefits
Job Training & Conferences
Clearcover offers a stipend to each employee to invest as they choose in their own professional development.
Diversity Program
Lunch and learns
Cross functional training encouraged
Promote from within
Time allotted for learning
Online course subscriptions available

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